#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/44/7154425.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7154425
loop_
_publ_author_name
'de la Fuente, Alex'
'Mena-Barragán, Teresa'
'Farrar-Tobar, Ronald A'
'Verdaguer, Xavier'
'García Fernández, José M'
'Ortiz Mellet, Carmen'
'Riera, Antoni'
_publ_section_title
;
 Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc)
 and ureido-DNJNAc derivatives as new hexosaminidase inhibitors.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6500
_journal_page_last               6510
_journal_paper_doi               10.1039/c5ob00507h
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H16 N4 O4'
_chemical_formula_weight         304.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-03-12 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1008(19)
_cell_length_b                   9.745(2)
_cell_length_c                   18.180(4)
_cell_measurement_reflns_used    6479
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.27
_cell_measurement_theta_min      2.37
_cell_volume                     1435.2(5)
_computing_cell_refinement       'Bruker APEX2 v2009.1-0'
_computing_data_collection       'Bruker APEX2 v2009.1-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17453
_diffrn_reflns_theta_full        36.57
_diffrn_reflns_theta_max         36.57
_diffrn_reflns_theta_min         2.24
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           70
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         7016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1420
_reflns_number_gt                6050
_reflns_number_total             7016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00507h2.cif
_cod_data_source_block           mo_af115_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_diffrn_measurement_specimen_suppport' tag replaced with
'_diffrn_measurement_specimen_support' tag as specified in the
replacement file
'/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 3376 2015-05-07 07:48:27Z andrius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154425--7154426.cif.
;
_cod_original_cell_volume        1435.2(6)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7154425
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.17864(11) 0.42447(9) -0.02137(5) 0.02024(15) Uani 1 1 d .
C2 C -0.07604(13) 0.50484(12) 0.08790(6) 0.02698(19) Uani 1 1 d .
H2A H -0.1014 0.4534 0.1335 0.032 Uiso 1 1 calc R
H2B H -0.0472 0.6004 0.1011 0.032 Uiso 1 1 calc R
C3 C 0.06568(12) 0.43658(9) 0.04591(5) 0.02041(15) Uani 1 1 d .
H3 H 0.1171 0.3625 0.0763 0.024 Uiso 1 1 calc R
C4 C 0.19688(11) 0.53563(9) 0.01810(5) 0.01937(15) Uani 1 1 d .
H4 H 0.1423 0.6148 -0.0071 0.023 Uiso 1 1 calc R
C5 C 0.30936(11) 0.46186(9) -0.03621(6) 0.02140(16) Uani 1 1 d .
H5 H 0.3657 0.3841 -0.0106 0.026 Uiso 1 1 calc R
C6 C 0.20792(12) 0.40522(10) -0.10073(5) 0.02152(16) Uani 1 1 d .
H6 H 0.1633 0.4832 -0.1305 0.026 Uiso 1 1 calc R
C7 C 0.06599(12) 0.31301(10) -0.07621(5) 0.02175(16) Uani 1 1 d .
H7A H -0.0100 0.2969 -0.1180 0.026 Uiso 1 1 calc R
H7B H 0.1098 0.2232 -0.0599 0.026 Uiso 1 1 calc R
C8 C 0.3138(2) 0.72867(12) 0.07739(8) 0.0398(3) Uani 1 1 d .
H8A H 0.2073 0.7785 0.0778 0.048 Uiso 1 1 calc R
H8B H 0.3722 0.7516 0.0312 0.048 Uiso 1 1 calc R
C9 C 0.41649(15) 0.77198(10) 0.14231(6) 0.02585(19) Uani 1 1 d .
C10 C 0.35035(19) 0.86053(15) 0.19398(9) 0.0421(3) Uani 1 1 d .
H10 H 0.2395 0.8911 0.1894 0.050 Uiso 1 1 calc R
C11 C 0.4469(3) 0.90471(16) 0.25282(9) 0.0586(6) Uani 1 1 d .
H11 H 0.4014 0.9652 0.2884 0.070 Uiso 1 1 calc R
C12 C 0.6085(3) 0.86107(16) 0.25974(8) 0.0521(5) Uani 1 1 d .
H12 H 0.6743 0.8917 0.2998 0.063 Uiso 1 1 calc R
C13 C 0.6732(2) 0.77296(16) 0.20823(9) 0.0462(4) Uani 1 1 d .
H13 H 0.7838 0.7417 0.2130 0.055 Uiso 1 1 calc R
C14 C 0.57798(17) 0.72954(12) 0.14951(7) 0.0316(2) Uani 1 1 d .
H14 H 0.6244 0.6698 0.1138 0.038 Uiso 1 1 calc R
N1 N -0.02250(10) 0.37780(9) -0.01632(5) 0.02047(14) Uani 1 1 d .
N2 N 0.31563(13) 0.31885(11) -0.14764(6) 0.0319(2) Uani 1 1 d .
N3 N 0.38938(15) 0.38163(14) -0.19657(6) 0.0385(3) Uani 1 1 d .
N4 N 0.4639(2) 0.4260(2) -0.24346(9) 0.0637(5) Uani 1 1 d .
O1 O -0.27950(9) 0.40179(9) -0.06950(5) 0.02706(15) Uani 1 1 d .
O2 O -0.21546(10) 0.50220(9) 0.03810(4) 0.02574(15) Uani 1 1 d .
O3 O 0.28435(10) 0.58387(7) 0.08077(4) 0.02349(14) Uani 1 1 d .
O4 O 0.42991(10) 0.55370(9) -0.06358(6) 0.03030(17) Uani 1 1 d .
H4A H 0.5226 0.5151 -0.0636 0.045 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 N1 128.16(9)
O1 C1 O2 121.86(9)
N1 C1 O2 109.96(8)
O2 C2 C3 105.39(8)
N1 C3 C4 109.52(8)
N1 C3 C2 100.99(8)
C4 C3 C2 114.44(8)
O3 C4 C3 106.95(7)
O3 C4 C5 112.16(8)
C3 C4 C5 109.49(7)
O4 C5 C4 110.01(8)
O4 C5 C6 109.16(8)
C4 C5 C6 110.16(7)
N2 C6 C7 106.09(9)
N2 C6 C5 109.19(8)
C7 C6 C5 113.08(8)
N1 C7 C6 109.62(8)
O3 C8 C9 109.55(9)
C14 C9 C10 119.35(12)
C14 C9 C8 121.02(12)
C10 C9 C8 119.57(12)
C9 C10 C11 119.77(14)
C12 C11 C10 120.44(13)
C13 C12 C11 119.43(14)
C12 C13 C14 120.28(16)
C9 C14 C13 120.72(13)
C1 N1 C7 124.10(8)
C1 N1 C3 112.39(8)
C7 N1 C3 120.86(8)
N3 N2 C6 114.72(11)
N4 N3 N2 172.65(16)
C1 O2 C2 109.74(8)
C4 O3 C8 111.98(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2173(12)
C1 N1 1.3472(12)
C1 O2 1.3534(12)
C2 O2 1.4478(14)
C2 C3 1.5308(15)
C3 N1 1.4555(12)
C3 C4 1.5221(13)
C4 O3 1.4217(12)
C4 C5 1.5239(14)
C5 O4 1.4150(12)
C5 C6 1.5349(14)
C6 N2 1.4823(14)
C6 C7 1.5258(14)
C7 N1 1.4485(13)
C8 O3 1.4324(14)
C8 C9 1.5045(17)
C9 C14 1.3783(17)
C9 C10 1.3835(17)
C10 C11 1.394(3)
C11 C12 1.382(3)
C12 C13 1.374(3)
C13 C14 1.3832(19)
N2 N3 1.2339(16)
N3 N4 1.1307(18)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 C2 C3 N1 -11.76(10)
O2 C2 C3 C4 105.77(9)
N1 C3 C4 O3 -176.93(7)
C2 C3 C4 O3 70.53(10)
N1 C3 C4 C5 -55.18(9)
C2 C3 C4 C5 -167.72(8)
O3 C4 C5 O4 -62.60(10)
C3 C4 C5 O4 178.84(8)
O3 C4 C5 C6 177.01(7)
C3 C4 C5 C6 58.45(9)
O4 C5 C6 N2 66.39(10)
C4 C5 C6 N2 -172.71(8)
O4 C5 C6 C7 -175.75(8)
C4 C5 C6 C7 -54.85(10)
N2 C6 C7 N1 166.04(8)
C5 C6 C7 N1 46.38(10)
O3 C8 C9 C14 67.10(16)
O3 C8 C9 C10 -115.73(13)
C14 C9 C10 C11 -0.54(19)
C8 C9 C10 C11 -177.77(12)
C9 C10 C11 C12 0.2(2)
C10 C11 C12 C13 -0.3(2)
C11 C12 C13 C14 0.7(2)
C10 C9 C14 C13 0.93(18)
C8 C9 C14 C13 178.12(11)
C12 C13 C14 C9 -1.0(2)
O1 C1 N1 C7 13.36(16)
O2 C1 N1 C7 -168.30(9)
O1 C1 N1 C3 174.94(9)
O2 C1 N1 C3 -6.71(11)
C6 C7 N1 C1 112.65(10)
C6 C7 N1 C3 -47.46(11)
C4 C3 N1 C1 -109.55(9)
C2 C3 N1 C1 11.52(10)
C4 C3 N1 C7 52.71(11)
C2 C3 N1 C7 173.78(9)
C7 C6 N2 N3 149.45(11)
C5 C6 N2 N3 -88.39(12)
C6 N2 N3 N4 -180(100)
O1 C1 O2 C2 176.63(9)
N1 C1 O2 C2 -1.83(11)
C3 C2 O2 C1 8.93(11)
C3 C4 O3 C8 -136.74(10)
C5 C4 O3 C8 103.21(11)
C9 C8 O3 C4 -176.12(10)
